131-08-8

Basic information

• Product Name: Sodium anthraquinone-2-sulfonate
• Synonyms: SODIUM ANTHRAQUINONE-BETA-SULFONATE;SODIUM ANTHRAQUINONE-B-SULFONATE;SODIUM ANTHRAQUINONE-2-SULFONATE;2-Anthracenesulfonicacid,9,10-dihydro-9,10-dioxo-,sodiumsalt;2-anthraquinonesulfonatesodium;9,10-anthraquinone-2-sodiumsulfonate;9,10-dihydro-9,10-dioxo-2-anthracenesulfonicacisodiumsalt;anthraquinone-2-sulfonatesodiumsalt
• CAS NO: 131-08-8
• Molecular Formula: C₁₄H₇O₅S*Na
• Molecular Weight: 310.26
• EINECS: 205-009-5
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones;Anthraquinonesulfonic Acids;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonates/Sulfinates;Sulfur Compounds
• Mol File: 131-08-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: beige powder
• Density: g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Store below +30°C.
• Water Solubility: Soluble in hot water, cold water and insoluble in alcohol or ether.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3580452
• CAS DataBase Reference: Sodium anthraquinone-2-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium anthraquinone-2-sulfonate(131-08-8)
• EPA Substance Registry System: Sodium anthraquinone-2-sulfonate(131-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CB1095550
• TSCA: Yes
• Hazardous Substances Data: 131-08-8(Hazardous Substances Data)

Usage

Chemical Properties

beige powder

Flammability and Explosibility

Notclassified

Purification Methods

It crystallises from H2O or MeOH (charcoal). [Costa and Bookfield J Chem Soc, Faraday Trans 1 82 991 1986, Beilstein 11 IV 671.]

InChI:InChI=1/C14H8O5S.Na/c15-13-9-3-1-2-4-10(9)14(16)12-7-8(20(17,18)19)5-6-11(12)13;/h1-7H,(H,17,18,19);/q;+1/p-1

Synthetic route

sodium anthraquinone-2-sulfonate (131-08-8) → AQDSNH4 (55922-85-5)

Conditions	Yield
Stage #1: sodium anthraquinone-2-sulfonate In water Stage #2: With ammonium hydroxide In water	98%

sodium anthraquinone-2-sulfonate (131-08-8) → 9,10-dioxo-9,10-dihydro-2-anthracenesulfonyl chloride (2381-23-9)

Conditions	Yield
With trichlorophosphate for 4h; Heating;	95%
With phosphorus pentachloride at 120℃; for 0.5h;	91.7%
With phosphorus pentachloride at 120℃; for 0.5h;	91%

copper(II) chloride monohydrate + sodium anthraquinone-2-sulfonate (131-08-8) + 2,9-bis(trifluoromethyl)-1,10-phenanthroline (147315-44-4) → [Cu(2,9-bis(trifluoromethyl)-1,10-phenanthroline)2][9,10-anthraquinone-2-sulfonate]*CH3CN (833458-03-0)

Conditions	Yield
With L-ascorbic acid In water; acetonitrile Cu-salt, Na-anthraquinonesulfonate and L-ascorbic acid were dissolved inhot (80°C) water, phenanthroline-compound in acetonitrile was ad ded, the soln. was stirred for 20 min at 80°C, cooled to room temp.; ppt. was filtered, dried in air; crystd. by vapor diffusion of diethyl ether into the acetonitrile-soln.;	90%

copper(II) tetrafluroborate hexahydrate + sodium anthraquinone-2-sulfonate (131-08-8) + 2,9-bis(trifluoromethyl)-1,10-phenanthroline (147315-44-4) → [Cu(2,9-bis(trifluoromethyl)-1,10-phenanthroline)2][9,10-anthraquinone-2-sulfonate]0.75[BF4]0.25*0.5H2O

Conditions	Yield
With L-ascorbic acid In water; acetonitrile Cu-salt, Na-anthraquinonesulfonate and L-ascorbic acid were dissolved inhot (80°C) water, phenanthroline-compound in acetonitrile was ad ded, the soln. was stirred for 20 min at 80°C, cooled to room temp.; ppt. was filtered, dried in air; crystd. by vapor diffusion of diethyl ether into the acetonitrile-soln.;	90%

sodium anthraquinone-2-sulfonate (131-08-8) → anthracene-2-sulfonic acid potassium salt (66601-71-6)

Conditions	Yield
Stage #1: sodium anthraquinone-2-sulfonate With ammonium carbonate In water at 80℃; Stage #2: With hydrogenchloride; zinc In water at 80℃; for 72h; Further stages;	87%

2.9-dimethyl-1,10-phenanthroline (484-11-7) + copper(II) tetrafluroborate hexahydrate + sodium anthraquinone-2-sulfonate (131-08-8) → bis(2,9-dimethyl-1,10-phenanthroline)copper(I) 9,10-anthraquinone-2-sulfonate (645389-00-0)

Conditions	Yield
With L-ascorbic acid In ethanol; water stoich. amt. of Na salt and Cu salt dissolved in H2O at 70°C; stoich. amt. of ligand in EtOH added; ascorbic acid added; stirred at 70°C for 2 h; cooled to room temp.; filtered; solid washed with Et2O; dried in air;	86%

copper(II) choride dihydrate + 2,11-diisopropyl-1,12-diazaperylene (1227480-20-7) + sodium anthraquinone-2-sulfonate (131-08-8) → bis(2,11-diisopropyl-1,12-diazaperylene)copper(I) 9,10-dihydro-9,10-dioxo-2-anthracenesulfonate (1227480-28-5)

Conditions	Yield
With sodium ascorbate In ethanol; chloroform; water N2; aq. soln. of CuCl2 (0.25 mmol) added to EtOH/CHCl3 (2/1) soln. of ligand (0.5 mmol), mixt. stirred for 20 min at room temp., sodium ascorbate (0.75 mmol) in EtOH/H2O (3/1) added, stirred for 1 h, aq. soln. of NaAQSO3 (1.5 mmol) added; CHCl3 evapd., ppt. filtered off, washed (water), dried (vac., CaCl2), recrystd. (CH2Cl2/Et2O), elem. anal.;	75%

methanol (67-56-1) + sodium anthraquinone-2-sulfonate (131-08-8) → 2-methoxy-9,10-anthraquinone (3274-20-2)

Conditions	Yield
With alkali hydroxide at 130℃; unter Druck;

potassium phenolate (100-67-4) + sodium anthraquinone-2-sulfonate (131-08-8) → 2-phenoxyanthraquinone (17613-71-7)

Conditions	Yield
at 200℃;

sodium anthraquinone-2-sulfonate (131-08-8) → 2-hydroxy-9,10-anthraquinone (605-32-3)

Conditions	Yield
With sodium hydroxide at 160 - 165℃; unter Druck; man loest die Schmelze in Wasser, faellt siedend heiss mit Salzsaeure, filtriert und behandelt den Niederschlag mit siedender Barytloesung, um Alizarin abzuscheiden; die erkaltete Barytloesung faellt man mit Salzsaeure;

sodium anthraquinone-2-sulfonate (131-08-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide; ethanol beim nachfolgende Luftoxydation;

sodium anthraquinone-2-sulfonate (131-08-8) → 2-chloroanthracene-9,10-dione (131-09-9)

Conditions	Yield
With hydrogenchloride Sonnenlicht;
With hydrogenchloride; sodium chlorate at 100℃;

sodium anthraquinone-2-sulfonate (131-08-8) → 9,10-anthracendiol-2-monosulfonic acid (16267-71-3)

Conditions	Yield
With iron at 85℃; Electrolysis;
With rongalite

sodium anthraquinone-2-sulfonate (131-08-8) → 1,7-dihydroxy-anthraquinone (569-08-4)

Conditions	Yield
With mercuri sulfate; sulfuric acid Erhitzen die Sufonsaeure mit Kalkmilch unter Druck;
With mercuri sulfate; sulfuric acid Erhitzen die Sufonsaeure mit Kalkmilch unter Druck;

sodium anthraquinone-2-sulfonate (131-08-8) → 5-nitro-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (6483-86-9) + 1-nitroanthraquinone-7-sulphonic acid (70094-11-0)

Conditions	Yield
With sulfuric acid; nitric acid

sodium anthraquinone-2-sulfonate (131-08-8) → 9,10-dihydro-anthracene-2-sulfonic acid

Conditions	Yield
With phosphorus; hydrogen iodide

sodium anthraquinone-2-sulfonate (131-08-8) → 2-aminoanthraquinone (117-79-3)

Conditions	Yield
With ammonia; sodium chloride; calcium chloride at 105℃; unter Druck;
With ammonia; calcium chloride; magnesium chloride at 105℃; unter Druck;
With sodium nitrate; ammonium chloride; ammonia

sodium anthraquinone-2-sulfonate (131-08-8) + p-toluidine (106-49-0) → 2-p-toluidino-anthraquinone (52869-12-2)

Conditions	Yield
With sodium hydroxide; air

sodium anthraquinone-2-sulfonate (131-08-8) + 4-chloro-aniline (106-47-8) → 2-(4-chloro-anilino)-anthraquinone

Conditions	Yield
With sodium hydroxide; air

sodium anthraquinone-2-sulfonate (131-08-8) + aniline (62-53-3) → 2-phenylaminoanthraquinone (36339-31-8)

Conditions	Yield
With sodium hydroxide

sodium anthraquinone-2-sulfonate (131-08-8) + dimethyl sulfate (77-78-1) → anthraquinone-2-methylsulfonate (106128-51-2)

Conditions	Yield
at 160 - 170℃;

sodium anthraquinone-2-sulfonate (131-08-8) + 2-aminoanthraquinone (117-79-3) → 2,2'-imino-di-anthraquinone (572-82-7)

Conditions	Yield
With alkali carbonate

sodium anthraquinone-2-sulfonate (131-08-8) + diallyl-phenyl-phosphane (29949-75-5) → Diallyl-phenyl-aminophosphonium

Conditions	Yield
(i) NH2Cl, NH3, Et2O, (ii) /BRN= 3580452/; Multistep reaction;

sodium anthraquinone-2-sulfonate (131-08-8) → sodium 1-hydroxyanthraquinone-2-sulphonate (36287-93-1)

Conditions	Yield
With water Mechanism; Irradiation;
With water Irradiation;
With dihydrogen peroxide Irradiation;

sodium anthraquinone-2-sulfonate (131-08-8) → C14H7O5S(2-) (41887-13-2, 79553-42-7) + 2-Hydroxy-9,10-anthrachinon-7-sulfonat + 8-Hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid anion + C14H8O5S(1-)

Conditions	Yield
In water Quantum yield; Product distribution; Irradiation; anaerobic conditions, different pH, with different additives as well;

sodium anthraquinone-2-sulfonate (131-08-8) → 9,10-anthraquinone-2-sodiumsulphonate radical anion (7218-32-8, 41887-14-3, 68824-10-2, 84647-90-5, 111020-10-1)

Conditions	Yield
With sodium hydroxide; triethanolamine; Eosin Y In water; isopropyl alcohol Quantum yield; Irradiation;
With sulfite(2-) In water; acetonitrile Quantum yield;
With cysteine thiol; Zn-TPPyS; cetyltrimethylammonim bromide In water Quantum yield; Irradiation; var. of reagent;

sodium anthraquinone-2-sulfonate (131-08-8) → 9,10-anthraquinol-2-sodium sulphonate cation radical

Conditions	Yield
With fluorosulfonylchloride; fluorosulphonic acid at -20.1 - 4.9℃; Irradiation;

sodium anthraquinone-2-sulfonate (131-08-8) + dimethyl sulfate (77-78-1) → 9,10-dimethoxy-2-anthracenesulfonic acid sodium salt (67580-39-6)

Conditions	Yield
With sodium hydroxide; zinc In ethanol at 80℃;

sodium anthraquinone-2-sulfonate (131-08-8) → 7-chloro-1-nitro-anthraquinone (6337-83-3)

Conditions	Yield
(i) H2SO4, (ii) HNO3, H2SO4, (iii) aq. HCl, NaClO3; Multistep reaction;

sodium anthraquinone-2-sulfonate (131-08-8) → anthracene 2-monosulphonate sodium salt (16106-40-4)

Conditions	Yield
With ammonium hydroxide; zinc for 3h;
With ammonium hydroxide; zinc

Downstream Products

• 17613-71-7 2-phenoxyanthraquinone 
• 17407-98-6 anthracene-2-sulfonyl chloride 
• 791786-22-6 N-methyl-9,10-dioxoanthracene-2-sulfonamide 
• 20327-68-8 2-(methylamino)anthraquinone 
• 7475-47-0 9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid anilide 
• 121172-98-3 p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulphonate 
• 108428-21-3 2-<(antraquinone-2-sulfonyl)oxy>benzaldehyde 
• 569-10-8 1,6-dihydroxy-9,10-anthraquinone 
• 16106-40-4 anthracene 2-monosulphonate sodium salt 
• 6337-83-3 7-chloro-1-nitro-anthraquinone 
• 67580-39-6 9,10-dimethoxy-2-anthracenesulfonic acid sodium salt 
• 36339-31-8 2-phenylaminoanthraquinone 
• 52869-12-2 2-p-toluidino-anthraquinone 
• 117-79-3 2-aminoanthraquinone 

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